Organic Letters
Letter
Deffieux, D. Synlett 2008, 467. (e) Ochiai, M.; Miyamoto, K. Eur. J. Org.
Chem.2008,2008,4229.(f)Dohi,T.;Kita,Y.Chem.Commun.2009,2073.
(g) Uyanik, M.; Ishihara, K. Chem. Commun. 2009, 2086. (h) Ngatimin,
M.;Lupton, D.W.Aust.J.Chem. 2010,63,653.(i)Liang, H.;Ciufolini,M.
A. Angew. Chem., Int. Ed. 2011, 50, 11849. (j) Fernandez Gonzalez, D.;
́ ́
Benfatti, F.; Waser, J. ChemCatChem 2012, 4, 955. (k) Yusubov, M. S.;
Zhdankin, V. V. Curr. Org. Synth. 2012, 9, 247. (l) Farid, U.; Wirth, T. in
Present Address
Institut de Chimie des Substances Naturelles, CNRS UPR 2301,
́ ́
Universite Paris-Sud, Universite Paris-Saclay, 1 av. de la Terrasse,
91198 Gif-sur-Yvette Cedex, France
Notes
The authors declare no competing financial interest.
Asymmetric Synthesis II; Christmann, M., Brase, S., Eds.; Wiley−VCH:
̈
2012; p 197. (m) Brown, M.; Farid, U.; Wirth, T. Synlett 2013, 24, 424.
(n)Parra,A.;Reboredo,S.Chem.-Eur.J.2013,19,17244.(o)Singh,F.V.;
Wirth, T.Chem. -AsianJ. 2014,9,950.(p)Kumar, R.;Wirth, T.Top. Curr.
Chem. 2015, 373, 243. (q) Maertens, G.; L’Homme, C.; Canesi, S. Front.
Chem. 2015, 2, 115. (r) Yoshimura, A.; Yusubov, M. S.; Zhdankin, V. V.
Org. Biomol. Chem. 2016, 14, 4771. (s) Yoshimura, A.; Zhdankin, V. V.
Chem. Rev. 2016, 116, 3328. (t) Berthiol, F. Synthesis 2015, 47, 587.
(u)Jobin-DesLauriers,A.;Legault,C.Y.AsianJ.Org.Chem.2016,5,1078.
(6) Examples of enantioselective oxidative lactonization: (a) Woerly, E.
M.; Banik, S. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2016, 138, 13858.
(b) Bekkaye, M.; Masson, G. Synthesis 2016, 48, 302. (c) Murray, S. J.;
Ibrahim, H. Chem. Commun. 2015, 51, 2376. (d) Dohi, T.; Takenaga, N.;
Nakae, T.; Toyoda, Y.; Yamasaki, M.; Shiro, M.; Fujioka, H.; Maruyama,
A.; Kita, Y. J. Am. Chem. Soc. 2013, 135, 4558. (e) Uyanik, M.; Yasui, T.;
Ishihara,K.Tetrahedron2010,66,5841.(f)Uyanik,M.;Yasui,T.;Ishihara,
K. Angew. Chem., Int. Ed. 2010, 49, 2175. (g) Dohi, T.; Maruyama, A.;
Takenaga, N.;Senami,K.;Minamitsuji,Y.;Fujioka,H.;Caemmerer,S.B.;
Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 3787. (h) Guilbault, A.-A.;
Basdevant, B.; Wanie, V.; Legault, C. Y. J. Org. Chem. 2012, 77, 11283.
(i) Volp, K. A.;Harned, A. M. Chem. Commun. 2013, 49, 3001. (j)Brenet,
S.; Berthiol, F.; Einhorn, J. Eur. J. Org. Chem. 2013, 8094. (k) Rodriguez,
A.; Moran, W. J. Synthesis 2012, 44, 1178.
ACKNOWLEDGMENTS
■
We thank ICSN and CNRS for financial support and a doctoral
fellowship to A.D., C.G. and M.B. thank Saclay University for
the doctoral fellowships, and C.G. thanks Labex Charm3at for a
master fellowship.
REFERENCES
■
(1) (a) Seitz, M.; Reiser, O. Curr. Opin. Chem. Biol. 2005, 9, 285.
(b)Hoffmann, H. M. R.;Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
(c) Koch, S. S. C.; Chamberlain, A. R. In Studies in Natural Products
Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: New York, 1995; Vol.
16, p 687.
(2) For selected examples, see: (a) Dey, S.; Karabal, P. U.; Sudalai, A.
Synth. Commun. 2015, 45, 1559. (b) Kuilya, T. K.; Chatterjee, S.;
Goswami,R.K.Tetrahedron2014,70,2905.(c)Dake,G.R.;Fenster,E.E.;
Patrick, B. O. J. Org. Chem. 2008, 73, 6711. (d) Deng, L. S.; Huang, X. P.;
Zhao, G. J. Org. Chem. 2006, 71, 4625. (e) Wrona, I. E.; Gabarda, A. E.;
Evano, G.; Panek, J. S. J. Am. Chem. Soc. 2005, 127, 15026. (f) Shiro, Y.;
Kato, K.; Fujii, M.; Ida, Y.; Akita, H. Tetrahedron 2006, 62, 8687.
(g)Hanessian, S.;Brassard, M. Tetrahedron 2004, 60, 7621. (h)Myers, A.
G.; Siu, M.; Ren, F. J. Am. Chem. Soc. 2002, 124, 4230. (i) Gonzalez, I. C.;
Forsyth, C. J. J. Am. Chem. Soc. 2000, 122, 9099. (j)Minehan, T. G.;Kishi,
Y. Angew. Chem., Int. Ed. 1999, 38, 923. (k) Kobayashi, S.; Ueno, M.;
Suzuki,R.;Ishitani,H.;Kim,H.S.;Wataya,Y.J.Org.Chem.1999,64,6833.
(l) Tanaka, M.; Tomioka, K.; Koga, K. Tetrahedron 1994, 50, 12829.
(3)(a)Louafi,F.;Lorion,M.M.;Oble,J.;Poli,G. Synlett2015,26,2237.
(b) Sanyal, I.; Barman, P. D.; Banerjee, A. K. Tetrahedron Lett. 2015, 56,
789. (c) Saikia, B.; Devi, T. J.; Barua, N. C. Org. Biomol. Chem. 2013, 11,
905. (d) Erdbrink, H.; Czekelius, C. Synlett 2013, 24, 2383. (e) Reddy, R.
S.; Kiran, I. N. C.; Sudalai, A. Org. Biomol. Chem. 2012, 10, 3655.
(f) Hamamoto, H.; Suzuki, Y.; Takahashi, H.; Ikegami, S. Adv. Synth.
Catal. 2007, 349, 2685. (g) Jenkinson, S. F.; Harris, T.; Fleet, G. W. J.
Tetrahedron: Asymmetry 2004, 15, 2667. (h) Chiacchio, U.; Rescifina, A.;
Iannazzo, D.; Romeo, G. J. Org. Chem. 1999, 64, 28. (i)Ha, H. J.;Yoon, K.
N.; Lee, S. Y.; Park, Y. S.; Lim, M. S.; Yim, Y. G. J. Org. Chem. 1998, 63,
(7)(a)Takesue, T.;Fujita, M.;Sugimura, T.;Akutsu, H. Org. Lett. 2014,
16, 4634. (b) Fujita, M.; Yoshida, Y.; Miyata, K.; Wakisaka, A.; Sugimura,
T. Angew. Chem., Int. Ed. 2010, 49, 7068.
(8) Shimogaki, M.; Fujita, M.; Sugimura, T. Eur. J. Org. Chem. 2013,
2013, 7128.
(9) Cao, Y.; Zhang, X.; Lin, G.; Zhang-Negrerie, D.; Du, Y. Org. Lett.
2016, 18, 5580.
(10) (a) Carboni, A.; Dagousset, G.; Magnier, E.; Masson, G. Org. Lett.
2014, 16, 1240. (b) Bekkaye, M.; Su, Y.; Masson, G. Eur. J. Org. Chem.
2013, 2013, 3978.
(11) Dohi, T.; Yamaoka, N.; Kita, Y. Tetrahedron 2010, 66, 5775.
(12) For recent selected examples using a stoichiometric amount of
chiral hypervalent iodine, see: (a) Farid, U.; Wirth, T. Angew. Chem., Int.
Ed. 2012, 51, 3462. (b) Farid, U.; Malmedy, F.; Claveau, R.; Albers, L.;
Wirth, T. Angew. Chem., Int. Ed.2013,52,7018. (c)Shimogaki,M.;Fujita,
M.; Sugimura, T. Angew. Chem., Int. Ed. 2016, 55, 15797.
(13) For representative natural products bearing spirocyclic γ-lactones
and derivatives, see: (a) Ghantous, A.; Gali-Muhtasib, H.; Vuorela, H.;
Saliba, N. A.; Darwiche, N. Drug Discovery Today 2010, 15, 668.
(b) Bunyapaiboonsri, T.; Yoiprommarat, S.; Intereya, K.; Rachtawee, P.;
Hywel-Jones, N. L.; Isaka, M. J. Nat. Prod. 2009, 72, 756.
(14) (a) Mizar, P.; Laverny, A.; El-Sherbini, M.; Farid, U.; Brown, M.;
Malmedy, F.; Wirth, T. Chem. - Eur. J. 2014, 20, 9910. (b) Pu, Y.; Gao, L.;
Liu, H.; Yan, J. Synthesis 2012, 44, 99. (c) Hirt, U. H.; Schuster, M. F. H.;
French, A. N.;Wiest, O. G.;Wirth, T. Eur. J. Org. Chem. 2001, 2001, 1569.
(d) Hirt, U. H.; Spingler, B.; Wirth, T. J. Org. Chem. 1998, 63, 7674.
(e) Koser, G. F.; Lodaya, J. S.; Ray, D. G.; Kokil, P. B. J. Am. Chem. Soc.
1988, 110, 2987. (f) Wirth, T.; Hirt, U. H. Tetrahedron: Asymmetry 1997,
8, 23. (g) Xia, M.; Chen, Z.-C. Synth. Commun. 1997, 27, 1315.
(h)Rebrovic,L.;Koser,G.F.J.Org.Chem.1984,49,2462.(i)Koser,G.F.;
Relenyi, A. G.; Kalos, A. N.; Rebrovic, L.; Wettach, R. H. J. Org. Chem.
1982, 47, 2487.
8062. (j)Harcken, C.;Bruckner, R.;Rank, E. Chem. -Eur. J. 1998, 4, 2342.
̈
(k)Ha,H.J.;Yoon,K.N.;Lee,S.Y.;Park,Y.S.;Lim,M.S.;Yim,Y.G.J.Org.
Chem. 1998, 63, 8062. (l) Okabe, M.; Sun, R. C.; Zenchoff, G. B. J. Org.
Chem. 1991, 56, 4392.
(4) Selected examples of carboxyloxylactonization: (a) Uyanik, M.;
Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
(b)Kang,Y.B.;Gade,L.H.J.Am.Chem.Soc.2011,133,3658.(c)Zhu,M.;
Sun, N. B.; Li, H.; Yan, Ji. J. Heterocycl. Chem. 2010, 47, 436. (d) Uyanik,
M.; Yasui, T.; Ishihara, K. Bioorg. Med. Chem. Lett. 2009, 19, 3848.
(e) Zhou, Z. S.; He, X. H. Tetrahedron Lett. 2010, 51, 2480. (f) Dohi, T.;
Takenaga, N.; Goto, A.; Maruyama, A.; Kita, Y. Org. Lett. 2007, 9, 3129.
(g) Boye, A. C.; Meyer, D.; Ingison, C. K.; French, A. N.; Wirth, T. Org.
Lett. 2003, 5, 2157. Selected examples of sulfonyloxylactonization:
(h) Yan, J.; Wang, H.; Yang, Z.; He, Y. Synlett 2009, 2669. (i) Shah, M.;
Taschner,M.J.;Koser,G.F.;Rach,N.L.TetrahedronLett.1986,27,4557.
(j)Hu,J.;Zhu,M.;Xu, Y.;Yan, J. Helv. Chim. Acta2014, 97, 137. Selected
examples of phosphoryloxylactonization: (k) Zhou, Z. S.; He, X. H.
Tetrahedron Lett. 2010, 51, 2480. (l) Koser, G. F.; Lodaya, J. T. S.; Ray, D.
G.; Kokil, P. B. J. Am. Chem. Soc. 1988, 110, 2987. (m) Zhou, Z. S.; He, X.
H. J. Chem. Res. 2014, 38, 630.
(15) (a) Haubenreisser, S.; Woste, T. H.; Martínez, C.; Ishihara, K.;
̈
Muniz, K. Angew. Chem., Int. Ed. 2016, 55, 413. (b) Woste, T.; Muniz, K.
Synthesis 2016, 48, 816.
̃
̈
̃
(5)Forselected reviewsonhypervalent iodinechemistry, see:(a)Ortiz,
(16) The formation of a hydrogen bond between the amide and ligands
attached to the iodine atom cannot be excluded (see SI and ref 15),
although a comparable ee was observed in the case of tertiary amide
precatalysts 11c and 11d.
́ ́ ́
F. L.; Iglesias, M. J.; Fernandez, I.; Sanchez, C. M. A.; Ruiz-Gomez, G.
Chem. Rev. 2007, 107, 1580. (b) Ciufolini, M. A.; Braun, N. A.; Canesi, S.;
Ousmer,M.;Chang,J.;Chai,D.Synthesis2007,3759.(c)Zhdankin,V.V.;
́
Stang, P. J. Chem. Rev. 2008, 108, 5299. (d) Quideau, S.; Pouysegu, L.;
D
Org. Lett. XXXX, XXX, XXX−XXX